tigogenin (BioDeep_00000000536)

   

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


(2aS,2R,4S,5R,6aS,6bS,8aS,8bR,9S,11aS,12aS,12bR)-5,6a,8a,9-Tetramethyldocosahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-10,2-pyran]-4-ol

化学式: C27H44O3 (416.3290274)
中文名称: 剑麻皂素, 知母皂苷元, 剑麻皂苷元
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 13.33%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@@H](O)C1)CC[C@@H](C)CO6)C
InChI: InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

描述信息

Tigogenin is a widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs. It has a role as a gout suppressant and a plant metabolite.
Tigogenin is a natural product found in Cordyline australis, Yucca gloriosa, and other organisms with data available.
A widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs.
Tigogenin, also known as sarsasapogenin, (3beta,5alpha,25s)-isomer or smilagenin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, tigogenin is considered to be a sterol lipid molecule. Tigogenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Tigogenin can be found in fenugreek, which makes tigogenin a potential biomarker for the consumption of this food product.
Tigogenin, one of steroidal sapogenins, is widely used for synthesizing steroid agents. Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells[1].
Tigogenin, one of steroidal sapogenins, is widely used for synthesizing steroid agents. Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells[1].

同义名列表

40 个代谢物同义名

(2aS,2R,4S,5R,6aS,6bS,8aS,8bR,9S,11aS,12aS,12bR)-5,6a,8a,9-Tetramethyldocosahydrospiro[naphtho[2,1:4,5]indeno[2,1-b]furan-10,2-pyran]-4-ol; (1R,2R,2S,4S,5R,7S,8R,9S,12S,13S,16S,18S)-5,7,9,13-tetramethyl-5-oxaspiro[oxane-2,6-pentacyclo[10.8.0.0?,?.0?,?.0??,??]icosane]-16-ol; (1R,2S,4S,5R,6R,7S,8R,9S,12S,13S,16S,18S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2-oxane]-16-ol; TIGOGENIN 90\\%; (25R)-5-alpha-spirostan-3-beta-ol; sarsasapogenin, (3beta,5alpha,25S)-isomer; sarsasapogenin, (3beta,5alpha,25R)-isomer; sarsasapogenin, (3beta,5beta,25S)-isomer; sarsasapogenin, (3beta,5beta,25R)-isomer; sarsasapogenin, (3beta,5beta)-isomer; 5-alpha-Spirostan-3-beta-ol, (25R)-; (25R)-5.alpha.-Spirostan-3.beta.-ol; Spirostan-3-ol, (3beta,5alpha,25R)-; (3-beta,5-alpha,25R)-Spirostan-3-ol; (3-beta,5alpha,25R)-spirostan-3-ol; 5alpha-Spirostan-3beta-ol, (25R)-; (3beta,5alpha,25R)-spirostan-3-ol; (25R)-5alpha-Spirostan-3beta-ol; (5alpha,25R)-Spirostan-3beta-ol; Spirostan-3-ol, (3b,5a,25R)-; GMBQZIIUCVWOCD-MFRNJXNGSA-N; 5-alpha-Spirostan-3-beta-ol; 22-Isoallospirostan-3|A-ol; (25R)-5a-Spirostan-3b-ol; 5,6-Dihydrodiosgenin; 5-epi-sarsasapogenin; epi-sarsasapogenin; UNII-4SMU15RR44; TIGOGENIN [MI]; Sarsasapogenin; epismilagenin; smilagenin; ST 27:2;O3; sarsaponin; 4SMU15RR44; tigogenin; TICOGENIN; (1R,2S,4S,6R,7S,8R,9S,12S,13S)-5,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2-oxane]-16-ol; GMBQZIIUCVWOCD-NRBCCYJRSA-N; Spirostan-3-ol; Tigogenin



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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PharmGKB(0)

242 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Shuangshuang Yang, Lei Fan, Rui Zhang, Chenghuan Song, Jiyun Shi, Jing Wang, Pingao Zhang, Hao Wang, Yongfang Zhang. Smilagenin induces expression and epigenetic remodeling of BDNF in alzheimer's disease. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Sep; 118(?):154956. doi: 10.1016/j.phymed.2023.154956. [PMID: 37499345]
  • Yuan Dai, Panwang Liu, Wen Wen, Ping Li, Chen Yang, Ping Wang, Shijun Xu. Sarsasapogenin, a principal active component absorbed into blood of total saponins of Anemarrhena, attenuates proliferation and invasion in rheumatoid arthritis fibroblast-like synoviocytes through downregulating PKM2 inhibited pathological glycolysis. Phytotherapy research : PTR. 2023 Jan; ?(?):. doi: 10.1002/ptr.7712. [PMID: 36631974]
  • Xi-Zhi Li, Hong Jiang, Liu Xu, Yi-Qi Liu, Jia-Wei Tang, Jia-Sen Shi, Xiu-Juan Yu, Xue Wang, Lei Du, Qian Lu, Cheng-Lin Li, Yao-Wu Liu, Xiao-Xing Yin. Sarsasapogenin restores podocyte autophagy in diabetic nephropathy by targeting GSK3β signaling pathway. Biochemical pharmacology. 2021 10; 192(?):114675. doi: 10.1016/j.bcp.2021.114675. [PMID: 34252407]
  • Deepa S Mandlik, Satish K Mandlik, Snehal Patel. Protective effect of sarsasapogenin in TNBS induced ulcerative colitis in rats associated with downregulation of pro-inflammatory mediators and oxidative stress. Immunopharmacology and immunotoxicology. 2021 Oct; 43(5):571-583. doi: 10.1080/08923973.2021.1955919. [PMID: 34338577]
  • Zuzana Bednarikova, Miroslav Gancar, Rui Wang, Lulu Zheng, Yun Tang, Yating Luo, Yan Huang, Barbora Spodniakova, Lei Ma, Zuzana Gazova. Extracts from Chinese herbs with anti-amyloid and neuroprotective activities. International journal of biological macromolecules. 2021 May; 179(?):475-484. doi: 10.1016/j.ijbiomac.2021.03.013. [PMID: 33675837]
  • Zhuang-Zhuang Tang, Yu-Meng Zhang, Ting Zheng, Ting-Ting Huang, Teng-Fei Ma, Yao-Wu Liu. Sarsasapogenin alleviates diabetic nephropathy through suppression of chronic inflammation by down-regulating PAR-1: In vivo and in vitro study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Nov; 78(?):153314. doi: 10.1016/j.phymed.2020.153314. [PMID: 32882582]
  • Yue Liu, Zhuang-Zhuang Tang, Yu-Meng Zhang, Li Kong, Wei-Fen Xiao, Teng-Fei Ma, Yao-Wu Liu. Thrombin/PAR-1 activation induces endothelial damages via NLRP1 inflammasome in gestational diabetes. Biochemical pharmacology. 2020 05; 175(?):113849. doi: 10.1016/j.bcp.2020.113849. [PMID: 32059841]
  • Deepa K Ingawale, Satish K Mandlik, Snehal S Patel. Combination of Sarsasapogenin and Fluticasone attenuates ovalbumin-induced airway inflammation in a mouse asthma model. Immunopharmacology and immunotoxicology. 2020 Apr; 42(2):128-137. doi: 10.1080/08923973.2020.1728541. [PMID: 32070162]
  • Lixia Pei, Yiyi Ye, Wenshu Zhao, Qun Ye, Songlan Ge, Zi-Wei Jiang, Xiao-Qiang Liang, Hai-Xian Gan, Lei Ma. A validated UPLC-MS/MS method for quantitative determination of a potent neuroprotective agent Sarsasapogenin-AA13 in rat plasma: Application to pharmacokinetic studies. Biomedical chromatography : BMC. 2020 Mar; 34(3):e4775. doi: 10.1002/bmc.4775. [PMID: 31845362]
  • Priya Kashyap, Kalaivani Muthusamy, Manisha Niranjan, Shweta Trikha, Suresh Kumar. Sarsasapogenin: A steroidal saponin from Asparagus racemosus as multi target directed ligand in Alzheimer's disease. Steroids. 2020 01; 153(?):108529. doi: 10.1016/j.steroids.2019.108529. [PMID: 31672628]
  • Shu Wang, Mengqi Liu, Wenbao Wang, Ting Li, Mengsuo Cui, Wenliang Sun, Xinggang Yang, Shaojiang Song. Preparation and Evaluation of mPEG-PLGA Block Copolymer Micelles Loaded with a Sarsasapogenin Derivative. AAPS PharmSciTech. 2019 Aug; 20(7):280. doi: 10.1208/s12249-019-1491-z. [PMID: 31399832]
  • Lixia Pei, Songlan Ge, Yiyi Ye, Ziwei Jiang, Xiaoqiang Liang, Wenshu Zhao, Lei Ma. Development and validation of a UPLC-MS/MS method for determination of Sarsasapogenin-AA22 in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2018 Oct; 32(10):e4295. doi: 10.1002/bmc.4295. [PMID: 29797524]
  • Yao-Wu Liu, Yun-Chao Hao, Ya-Jing Chen, Shen-Yuan Yin, Meng-Ya Zhang, Li Kong, Tao-Yun Wang. Protective effects of sarsasapogenin against early stage of diabetic nephropathy in rats. Phytotherapy research : PTR. 2018 Aug; 32(8):1574-1582. doi: 10.1002/ptr.6088. [PMID: 29682805]
  • Yi Zhang, Lijun Jin, Jinchang Liu, Wei Wang, Haiyang Yu, Jian Li, Qian Chen, Tao Wang. Effect and mechanism of dioscin from Dioscorea spongiosa on uric acid excretion in animal model of hyperuricemia. Journal of ethnopharmacology. 2018 Mar; 214(?):29-36. doi: 10.1016/j.jep.2017.12.004. [PMID: 29233733]
  • Bo Yang, Zhirui Liu, Jing Hu, Xiaodan Lai, Peiyuan Xia. Quantitative determination of sarsasapogenin in rat plasma using liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Jun; 1022(?):213-219. doi: 10.1016/j.jchromb.2016.04.020. [PMID: 27107248]
  • Rajarshi Sengupta, Amy Barone, Jayne Marasa, Sara Taylor, Erin Jackson, Nicole M Warrington, Shyam Rao, Albert H Kim, Jeffrey R Leonard, David Piwnica-Worms, Joshua B Rubin. Novel chemical library screen identifies naturally occurring plant products that specifically disrupt glioblastoma-endothelial cell interactions. Oncotarget. 2015 Jul; 6(21):18282-92. doi: 10.18632/oncotarget.4957. [PMID: 26286961]
  • Guo-long Li, Jie Yang, Jin-ao Duan, Hong-bo Liu, Zhen-hua Zhu, Da-wei Qian, Zhi-shu Tang. [Quality Analysis and Evaluation of Anemarrhena asphodeloides Rhizome from Different Habitats]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1148-52. doi: . [PMID: 26762052]
  • Xia Wu, Lei Wang, Guo-Cai Wang, Hui Wang, Yi Dai, Wen-Cai Ye, Yao-Lan Li. New steroidal saponins and sterol glycosides from Paris polyphylla var. yunnanensis. Planta medica. 2012 Oct; 78(15):1667-75. doi: 10.1055/s-0032-1315239. [PMID: 22923196]
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  • Mahenina Jaovita Manase, Anne-Claire Mitaine-Offer, David Pertuit, Tomofumi Miyamoto, Chiaki Tanaka, Stéphanie Delemasure, Patrick Dutartre, Jean-François Mirjolet, Olivier Duchamp, Marie-Aleth Lacaille-Dubois. Solanum incanum and S. heteracanthum as sources of biologically active steroid glycosides: confirmation of their synonymy. Fitoterapia. 2012 Sep; 83(6):1115-9. doi: 10.1016/j.fitote.2012.04.024. [PMID: 22579841]
  • Kee Dong Yoon, Young-Won Chin, Min Hye Yang, Janggyoo Choi, Jinwoong Kim. Application of high-speed countercurrent chromatography-evaporative light scattering detection for the separation of seven steroidal saponins from Dioscorea villosa. Phytochemical analysis : PCA. 2012 Sep; 23(5):462-8. doi: 10.1002/pca.2342. [PMID: 22407490]
  • Virginia Lanzotti, Elisa Barile, Vincenzo Antignani, Giuliano Bonanomi, Felice Scala. Antifungal saponins from bulbs of garlic, Allium sativum L. var. Voghiera. Phytochemistry. 2012 Jun; 78(?):126-34. doi: 10.1016/j.phytochem.2012.03.009. [PMID: 22513009]
  • R Zhang, Z Wang, P A Howson, Z Xia, S Zhou, E Wu, Z Xia, Y Hu. Smilagenin attenuates beta amyloid (25-35)-induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. Neuroscience. 2012 May; 210(?):275-85. doi: 10.1016/j.neuroscience.2012.03.017. [PMID: 22441042]
  • Xu Pang, Yue Cong, He-Shui Yu, Li-Ping Kang, Bing Feng, Bing-Xing Han, Yang Zhao, Cheng-Qi Xiong, Da-Wei Tan, Wei Song, Bin Liu, Yu-Wen Cong, Bai-Ping Ma. Spirostanol saponins derivated from the seeds of Trigonella foenum-graecum by β-glucosidase hydrolysis and their inhibitory effects on rat platelet aggregation. Planta medica. 2012 Feb; 78(3):276-85. doi: 10.1055/s-0031-1280373. [PMID: 22127545]
  • Shi-Fu Xiao, Hai-Bo Xue, Xia Li, Chao Chen, Guan-Jun Li, Cheng-Mei Yuan, Ming-Yuan Zhang. A double-blind, placebo-controlled study of traditional Chinese medicine sarsasapogenin added to risperidone in patients with negative symptoms dominated schizophrenia. Neuroscience bulletin. 2011 Aug; 27(4):258-68. doi: 10.1007/s12264-011-1417-6. [PMID: 21788997]
  • Sunil Kumar Upadhyay, Clinton C Creech, Katharine L Bowdy, Edwin D Stevens, Branko S Jursic, Donna M Neumann. Synthesis and antifungal activity of functionalized 2,3-spirostane isomers. Bioorganic & medicinal chemistry letters. 2011 May; 21(10):2826-31. doi: 10.1016/j.bmcl.2011.03.092. [PMID: 21489791]
  • Assunta Napolitano, Tamar Muzashvili, Angela Perrone, Cosimo Pizza, Ether Kemertelidze, Sonia Piacente. Steroidal glycosides from Ruscus ponticus. Phytochemistry. 2011 May; 72(7):651-61. doi: 10.1016/j.phytochem.2011.01.033. [PMID: 21354581]
  • Tabasum Sidiq, Anamika Khajuria, Pankaj Suden, Surjeet Singh, N K Satti, K A Suri, V K Srinivas, E Krishna, R K Johri. A novel sarsasapogenin glycoside from Asparagus racemosus elicits protective immune responses against HBsAg. Immunology letters. 2011 Mar; 135(1-2):129-35. doi: 10.1016/j.imlet.2010.10.013. [PMID: 21035507]
  • Jang-Gi Choi, Ok-Hwa Kang, Young-Seob Lee, Hee-Sung Chae, You-Chang Oh, Obiang-Obounou Brice, Min-San Kim, Dong-Hwan Sohn, Hun-Soo Kim, Hyun Park, Dong-Won Shin, Jung-Rae Rho, Dong-Yeul Kwon. In Vitro and In Vivo Antibacterial Activity of Punica granatum Peel Ethanol Extract against Salmonella. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):690518. doi: 10.1093/ecam/nep105. [PMID: 19687188]
  • Liwei Wang, Xiaodong Wang, Xiaofan Yuan, Bing Zhao. Simultaneous analysis of diosgenin and sarsasapogenin in Asparagus officinalis byproduct by thin-layer chromatography. Phytochemical analysis : PCA. 2011 Jan; 22(1):14-7. doi: 10.1002/pca.1244. [PMID: 20799270]
  • Zhong-Quan Zhang, Jian-Chao Chen, Jian Yan, Ming-Hua Qiu. Three steroids with unique structural feature of 5β-Spirostan-1β,3β,17α-trihydroxyl from Reineckia carnea. Chemical & pharmaceutical bulletin. 2011; 59(1):53-6. doi: 10.1248/cpb.59.53. [PMID: 21212547]
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  • Lasha Mskhiladze, Jean Legault, Serge Lavoie, Vakhtang Mshvildadze, Jumber Kuchukhidze, Riad Elias, André Pichette. Cytotoxic steroidal saponins from the flowers of Allium leucanthum. Molecules (Basel, Switzerland). 2008 Nov; 13(12):2925-34. doi: 10.3390/molecules13122925. [PMID: 19037184]
  • Yuanyuan Lu, Jianguang Luo, Deran Xu, Xuefeng Huang, Lingyi Kong. Characterization of spirostanol saponins in Solanum torvum by high-performance liquid chromatography/evaporative light scattering detector/electrospray ionization with multi-stage tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2008 Aug; 22(16):2447-52. doi: 10.1002/rcm.3630. [PMID: 18634112]
  • Xue-Feng Huang, Yu-Ying Lin, Ling-Yi Kong. Steroids from the roots of Asparagus officinalis and their cytotoxic activity. Journal of integrative plant biology. 2008 Jun; 50(6):717-22. doi: 10.1111/j.1744-7909.2008.00651.x. [PMID: 18713412]
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  • Bertrand Liagre, Pascale Vergne-Salle, David Y Leger, Jean-Louis Beneytout. Inhibition of human rheumatoid arthritis synovial cell survival by hecogenin and tigogenin is associated with increased apoptosis, p38 mitogen-activated protein kinase activity and upregulation of cyclooxygenase-2. International journal of molecular medicine. 2007 Oct; 20(4):451-60. doi: . [PMID: 17786275]
  • Yu Zhao, Li-Ping Kang, Yi-Xun Liu, Yang Zhao, Cheng-Qi Xiong, Bai-Ping Ma, Fang-Ting Dong. Three new steroidal saponins from the rhizome of Paris polyphylla. Magnetic resonance in chemistry : MRC. 2007 Sep; 45(9):739-44. doi: 10.1002/mrc.2039. [PMID: 17638316]
  • Juan Chen, Chong-jun Yang, Yu-hai Guo. [Studies on accumulation of active ingredients, N, P and K in Anemarrhena asphodeloides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Aug; 32(15):1504-7. doi: ". [PMID: 17972573]
  • Hua Zhou, Xi Yang, Naili Wang, Yaou Zhang, Guoping Cai. Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. Molecular and cellular endocrinology. 2007 May; 270(1-2):17-22. doi: 10.1016/j.mce.2007.01.017. [PMID: 17363141]
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